Ilicicolin A
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| Category | Antibiotics |
| Catalog number | BBF-01495 |
| CAS | 22581-06-2 |
| Molecular Weight | 390.94 |
| Molecular Formula | C23H31ClO3 |
| Purity | >98% |
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Description
Ilicicolin A is originally isolated from Cylinddrocladium ilicicola MFC-870. It inhibited Bacillus carbonifera with the concentration of 6 μg/mL and its toxic concentration to Hela cells was 0.2 μg/mL.
Specification
| Synonyms | LL-Z 1272-alpha; 3-chloro-4,6-dihydroxy-2-methyl-5-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)benzaldehyde |
| IUPAC Name | 5-chloro-2,4-dihydroxy-6-methyl-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzaldehyde |
| Canonical SMILES | CC1=C(C(=C(C(=C1Cl)O)CC=C(C)CCC=C(C)CCC=C(C)C)O)C=O |
| InChI | InChI=1S/C23H31ClO3/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-19-22(26)20(14-25)18(5)21(24)23(19)27/h8,10,12,14,26-27H,6-7,9,11,13H2,1-5H3/b16-10+,17-12+ |
| InChI Key | MHWOMRMBQGSTFS-JTCWOHKRSA-N |
Properties
| Appearance | Light Yellow Diamond Crystalline |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 72-72.5°C |
Reference Reading
1. A novel inhibitor of PGK1 suppresses the aerobic glycolysis and proliferation of hepatocellular carcinoma
Mingfeng Li, Aotong Zhang, Xin Qi, Rilei Yu, Jing Li Biomed Pharmacother. 2023 Feb;158:114115. doi: 10.1016/j.biopha.2022.114115. Epub 2022 Dec 12.
Phosphoglycerate kinase 1(PGK1) is an important enzyme in the metabolic glycolysis pathway. Nowadays, PGK1 is an appealing therapeutic target for multiple cancers. However, no effective inhibitor of PGK1 has been reported. In this study, we demonstrate that Ilicicolin H a 5-(4-hydroxyphenyl)-pyridone with a decalin ring system and a non-ATP-competitive inhibitor of PGK1, inhibits the proliferation and promotes apoptosis of Hepatocellular carcinoma (HCC). Many cancer cells display enhanced glycolysis which is critical for tumor development. Here we identified that Ilicicolin H can target PGK1 in vitro to inhibit the lactate production and glucose uptake of HCC cells. These findings suggest that the PGK1 inhibitor- Ilicicolin H is a promising anticancer agent and may provide a better therapeutic strategy for HCC treatment in the future.
2. Heterologous production of ascofuranone and ilicicolin A in Aspergillus sojae
Yasuko Araki, Yasutomo Shinohara, Seiichi Hara, Atsushi Sato, Ryoichi Sakaue, Keiko Gomi, Kiyoshi Kita, Kotaro Ito J Gen Appl Microbiol. 2022 Jun 20;68(1):10-16. doi: 10.2323/jgam.2021.08.001. Epub 2022 Apr 13.
Ascofuranone and its precursor, ilicicolin A, are secondary metabolites with various pharmacological activities that are produced by Acremonium egyptiacum. In particular, ascofuranone strongly inhibits trypanosome alternative oxidase and represents a potential drug candidate against African trypanosomiasis. However, difficulties associated with industrial production of ascofuranone by A. egyptiacum, specifically the co-production of ascochlorin, which inhibits mammalian respiratory chain complex III at low concentrations, has precluded its widespread application. Therefore, in this study, ascofuranone biosynthetic genes (ascA-E and H-J) were heterologously expressed in Aspergillus sojae, which produced very low-levels of endogenous secondary metabolites under conventional culture conditions. As a result, although we obtained transformants producing both ilicicolin A and ascofuranone, they were produced only when an adequate concentration of chloride ions was added to the medium. In addition, we succeeded in increasing the production of ilicicolin A, by enhancing the expression of the rate-determining enzyme AscD, using a multi-copy integration system. The heterologous expression approach described here afforded the production of both ascofuranone and ilicicolin A, allowing for their development as therapeutics.
3. Ilicicolin A Exerts Antitumor Effect in Castration-Resistant Prostate Cancer Via Suppressing EZH2 Signaling Pathway
Lang Guo, Xiaowei Luo, Ping Yang, Yanting Zhang, Jialuo Huang, Hong Wang, Yinfeng Guo, Weifeng Huang, Zhiqiang Chen, Shusheng Wang, Junjian Wang, Jinping Lei, Songtao Xiang, Yonghong Liu Front Pharmacol. 2021 Oct 27;12:723729. doi: 10.3389/fphar.2021.723729. eCollection 2021.
The Polycomb protein enhancer of zeste homolog 2 (EZH2) has critical roles in prostate cancer (PCa) progression and drug-resistance, which remains an obstacle for PCa treatment. Enzalutamide (ENZ) is a second-generation androgen receptor antagonist employed for treatment of metastatic castration-resistant prostate cancer A considerable proportion of tumors eventually develop resistance during treatment. Thus, agents that can overcome resistance to PCa are needed urgently. Ilicicolin A (Ili-A), an ascochlorin derivative isolated from the coral-derived fungus Acremonium sclerotigenum GXIMD 02501, shows antiproliferative activity in human PCa cells, but its mechanism of action against Castration-resistant prostate cancer is not known. Herein, RNA-sequencing showed the EZH2 pathway to be involved in PCa proliferation. Ili-A at low doses reduced the protein level of EZH2, leading to transcriptional change. Interestingly, Ili-A suppressed the binding of EZH2 to promoter regions in AR/serine/threonine polo-like kinase-1/aurora kinase A. Moreover, Ili-A could enhance the anticancer activity of enzalutamide in CRPC cancer models. These data suggest that Ili-A could be used in combination with enzalutamide to treat CRPC.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
